The Challenger Concept for Customer Success

These days, buyers have more choices, are better informed, and expect a superior customer experience.

As Customer Success Managers, we have a narrow margin to bring value to a customer, or else we risk losing them.  So, it’s not surprising that many Customer Success teams spend tremendous energy on keeping customers “happy” or doing whatever they can to adapt to customer desires.

The problem with this approach is that it assumes customers know what’s best.  In reality, Customer Success Managers are the authority on best practices with their tool / service.  If CSMs always bow to the requirements of the customer (who isn’t the product expert), the result is often a lack of success.

Have you had a customer churn because they refused to use your product in the manner that would produce the best results?  

Sometimes, a customer’s habits are the biggest hurdle to their success.  This is why “challenging” your customers can have a positive impact on retention and growth.


The Challenger Concept

The “challenger” concept was popularized as a sales strategy by Matthew Dixon & Brent Adamson in their book, The Challenger Sale.  In their view,  the sales landscape had fundamentally shifted, and prospects were now too busy, too well informed, and had too many options for a long-term relationship strategy to work.  Instead, Dixon and Adamson proposed consultative selling that wasn’t afraid to challenge the customer’s assumptions.

They broke the model into three steps:

  • Teach: Teach prospects how their product solves common industry challenges.
  • Tailor: Tailor the solution to the potential customer’s specific needs.
  • Take Control: Push the prospect by challenging their assumptions.

Although the challenger model was originally designed for sales, it also has a lot of application in Customer Success!


How to leverage the Challenger Concept for Customer Success

Today, customers increasingly expect that Customer Success will help them not only achieve value with a product but also impact their business as a whole.

As mentioned before, a customer’s habits can often be the roadblock to achieving success.  So, if that expected impact is what customers truly want (and for the most part it is), then we need to challenge them to modify their behavior and enact true change management.  Using the Challenger Sale strategies are a great place to start.

What does this mean in practice?

First, let’s understand the requirements for this strategy to work:

  • Be fully invested in the customer’s success – The challenger strategy is not about attacking customers, it is about positioning them for real long-term success.  You need to have their best interest in mind and need to be able to communicate that to them.
  • Learn best practices with your product – You have to be a product expert to begin to build trust and be seen as a consultant.
  • Understand their business – You and your team need to be able to understand the specific use-cases for their business and industry.  
  • Teach them something new – If you understand their use-case, then your product might show them a new way to think about their business.
  • Read the customer correctly – This strategy may not work with all customers.  There will be some who will react poorly to being challenged or are advanced enough that this strategy isn’t needed.
  • Share customer stories – Give real examples from other customers to illustrate your points and paint the right picture of success.

Once you have a foundation, “challenging” the customer comes down to getting them to change.  It may involve changing their processes, goals, preconceived notions, strategy, or anything you feel is currently inhibiting their success.  Some examples of areas to challenge customers are:

  • Pushing against their success criteria – Some customer’s expectations of your product can either be unrealistic or lacking enough detail to give you measurable ROI.
  • Scrutinizing bad workflows – Are customers using your product in a way you think fails to deliver value?  Be candid and let them know how their behavior will decrease the potential value they receive.  Give examples of the success other customers have seen following your best practices.
  • Addressing low engagement or usage – A customer who has low engagement has a low likelihood of success.  Be upfront and let them know that you are worried that they are not heading for success based on their engagement.  Confirm their expectations and compare that to their current path.

Finally, you have the foundation, you know what you want them to change, now you need to convince them to do so.  This is the most difficult part as it requires asking tough questions or voicing concerns that may produce some friction.  It’s important to conduct this part with respect and with the goal of helping them and their business.

Some examples of the types of questions or statements you can use are:

  • “You mentioned you want to be able to improve X, but how will you quantify and measure it?  In what time frame?”
  • “I understand your workflow is to do X, then Z, then Y, but from my experience, when customers have done that in the past they end up seeing less value.”
  • “You signed up to achieve X, but your team hasn’t logged in regularly since the beginning.  Most customers who don’t make our product a habit from the start won’t see an improvement in X.  Will you be able to work with me to get them engaged?”
  • “I’ve recently been working with customer X who is in a similar industry, and they’ve been successful in increasing Y.  You haven’t mentioned that as one of your criteria for success, but I think you should consider it as a future goal.”
  • I understand you want us to prioritize a new feature but it’s outside the scope of our product’s intended workflow. What is the fundamental business problem you are trying to address?

Do any of these hypothetical examples resonate with you?

The idea is to cut through unnecessary diplomacy and be honest with your customers.

To recap, concepts from the Challenger Sale can be repurposed to help Customer Success Managers deliver more value for their customers.  This strategy requires CSMs to be 1) invested in their customer’s success, 2) knowledgeable about their client’s business and use-case, and 3) able to teach customers something new.  With this foundation, CSMs can challenge misguided assumptions with thoughtful and pointed questions.


Will this work for me?

While it isn’t easy, “challenging” customers is a powerful tool in a CSMs arsenal to help customers whose biggest hurdle is their own behavior.


Originally posted on Natero’s blog

How We Re-Activate Dormant Customers

*Note*  Our customers are not subscribers, but use us on a transactional basis.  I think the principles still apply, but wanted to point that out.

Ideally as a CSM, you and each one of your customers form a strong relationship as you expertly guide them from success to success, and off into the glorious sunset.

The reality, is you’re going to have a lot of people who are distant, unresponsive, and eventually disappear.  Though it sucks, that is some people’s preferred interaction style, so what do you do when someone becomes dormant?  Do you rage, cry, shout obscenities at random strangers?

We thought about doing a few of these, but instead decided to combat dormant customers in two ways:  Setting up the relationship early in the customer lifetime and automating reactivation later by choosing criteria.

Screen Shot 2016-04-28 at 4.12.14 PM

Setting Up the Relationship Early

You need to accept that each relationship won’t be perfect…..deep breath, you can do it.  Ok, now it’s time to set expectations for the relationship.  

What we did was ask each customer the best way to get ahold of them (text, email, call, carrier pigeon, etc), and let them know that we will reach out if we think we can help them be more successful AND asked permission to contact them if we saw engagement drop off.

This provided a base to the relationship and the expectation that we would contact them when it was beneficial to them, NOT to just “check-in”.  It also gave us their preferred mode of contact.

Set Criteria for Reactivation

You need to decide how best to reach out to dormant customers and when you should do that.  Along with that, if you can automate any part of the process to reduce the time needed that is fantastic.

We realized with a large number of customers per CSM, it would be really hard to follow up with everyone in a customized way.  We decided to automate our attempts to reactivate accounts that had gone dormant as a first pass.

Our criteria was pretty straightforward.  If someone hadn’t engaged (logged in or posted a job) in 90 days, we would automate an email / text (not able to do this if the customer prefers a call) with basic personalization that offered them a discount on their next job posting.  

We’d also send a reply to that email if they hadn’t logged back in or replied in 2 days (always send a reply email to customers a day or two after if they don’t interact, it’s a great way to increase your response rate by a lot!).

Very simple criteria and setup!  The first email has a solid 28% open rate and the reply email has a 29% open rate.  The best part is that these emails get about 9% of all dormant accounts to re-activate and post a job!

After that, we can prioritize a more personalized outreach via phone or other channel, but automating it this way definitely saves us some time.
For us the most helpful things we did was setting up the relationship upfront, and automating part of the reactivation process to reduce time spent.

*These Customer Success posts are meant illustrate things we’ve learned at Proven, so they may not translate perfectly to your company / industry.  For context, the majority of our Saas customers are low LTV  “pro-sumers” who are generally SMBs*

Don’t Let Your Customer Evaluate Your Product Without You

Who knows your product and it’s values best?

Hopefully you answered yourself.  If not…..there might be bigger problems at hand.

When we first started bringing on customers, we figured we had a great product with a clear value prop.  We were getting some great feedback on it from a few happy first time users and we started researching the yachts we were all going to buy.

One thing I didn’t tell you is our first use was free for customers.  So when we sauntered back to them asking if they were ready to start paying, a LOT of them said no (cancel the yachts!).

When we dug deeper we found that a lot of people were evaluating our product on criteria that they shouldn’t have been.  For example, we are a job posting platform, but some people assumed that we were recruiters who were hand picking applicants for them.  This presented a clear problem due to a mismatch between how we viewed our product and how customers actually perceived it.

It is key to ensure that you guide the customer’s evaluation of your product.  

If you don’t you will have the equivalent of people trying to use a screwdriver to hammer in a nail.

If you don’t, you will have people using your product incorrectly, or not experiencing the full capabilities.  We’ve had customers complain that we lacked features that were ACTUAL FEATURES.  This was not their fault, this was our fault for not guiding their journey and giving them the tools to correctly evaluate us.

Our process for this started in when we created our Ideal Customer Profile.  Once we knew the type of outcomes our ICP was trying to achieve, we figured out how to position our product to solve those needs.  We then made sure sales and marketing were tailoring their pitches to ensure our messaging was aligned between all departments.

Then, when we were closing a new customer, we asked for their Desired Outcomes to make sure that they fit with our ICP.  If not?  We politely pointed them towards products we felt would suit their better needs.  Then we told them what to expect from our product, and how to gauge whether it was making them successful.  Lastly, a few days after they started using the product, we presented them with their ROI and a description of how the product was delivering as promised.

This change not only helped us ensure that people were correctly evaluating our product, but it made it easy for us to spot prospects who were going to be a bad fit, and nip future churn issues in the bud.

The takeaway?  Make sure your customers are using your scorecard to grade your product.

*These Customer Success posts are meant illustrate things we’ve learned at Proven, so they may not translate perfectly to your company / industry.  For context, the majority of our Saas customers are low LTV  “pro-sumers” who are generally SMBs*

How we find Desired Outcomes and show ROI

The Problem

We have a low touch, mostly self-serve Saas product.  It’s great because we don’t need a heavy sales component, and don’t have to worry about losing conversions to the enemy of all deals: time.

However, one of the negatives of such a product is that there’s often no conversation with the customer.  Couple this with the fact that they are not responsive to email, and this leaves us with a problem on how to know what they are trying to get out our product.

Finding the Desired Outcomes

As I’ve written previously, the solution we used was to build the capturing of Desired Outcomes into the product.  By using our past data (way back when we had no self-serve component and talked to all new customers), we identified the 4 most common DOs.  Then, we built a widget into the site as a component of onboarding to ask for their DO and to give us the ammo to make sure they are successful.

The other benefit is that we then know how best to present them ROI.  Our product can be helpful on a couple fronts (each one related to different desired outcome; Saving Time, More Applicants, Improved Collaboration, etc), so knowing how to present it correctly is very powerful.

The Presentation

Now that we know the DOs of the customer, we know how we want to frame their ROI.  The question became “how to we present it?”.  Keep in mind, we’re a small team, so we weren’t going to be able to use engineering for this problem, and, since we’re low touch, a scheduled phone call was unlikely.

To keep things simple, we decided to use Venngage to create some simple infographics that we could email a few days after customers had used the product for the first time.  We decided that 7 days after their first job posting was the best time to present them with their ROI.

This is an example of one of the infographics we use to present the time savings customers get from using us.  We did a quick formula to figure out how to get it in terms of dollars and came up with:

Screen Shot 2016-03-07 at 11.07.33 AM

Now this is pretty simplistic, however we’ve had some great feedback from customers who love seeing that their choice to try our service is giving them measurable success.  We got inspiration from other products such as Slack that send usage reports every month.  It’s our feeling that showing customers their own usage and data can be very powerful in getting them to further use and value the product.

It’s a manual process, and could be improved a thousand different ways, but we now have a system for capturing a customer’s Desired Outcome, and a way to show them that they are achieving that outcome while getting a measurable ROI.


*These Customer Success posts are meant illustrate things we’ve learned at Proven, so they may not translate perfectly to your company / industry.  For context, the majority of our Saas customers are low LTV  “pro-sumers” who are generally SMBs*

How to Schedule Kick-Off Calls

*Important note here.  This advice is for low touch products like ours.  For enterprise or mid market clients, this is probably a non-issue as kick-offs are very commonplace.*

One of the first things our CS team decided was that we didn’t want customer to evaluate our product on their own.  Once they had been sold on Proven as a SMB hiring solution to their issues, we wanted to make sure they used the platform in the best way possible and that we were their preliminary guide

We decided that we would do kick off calls with each new customer.  There were a few common sticking points for new users and we felt we should navigate them through those as well as some best practices (lack of bandwidth did allow us to fix this with product design at first).

Ok great, people will get closed by our sales team, then we’ll email them and find a time to hop on a quick 10 minute call and set them up for success!  Nope, not even close.  Maybe 1/4 of new customers actually did the kick off call and lots of those that missed it didn’t use some great features like our app or interview scheduler.


Eventually we got enough that had missed the kick-off to respond to our emails or talk to us on the phone to get some good feedback.  We found that they didn’t think the kick-off was important, and also felt that they were too busy for a call.

Our solution was to make scheduling the kick-off call part of the sales close.  After setting up the account, reps would be clear that the next step of the process was to schedule a call with their CS rep.  It was key to convey that the kick-off is a big part of the success they would have using us.  We used Doodle for the scheduling to make picking a time easy.

The result was bringing our kick-off call success rate to 50%!

The takeaway:  Impart the importance of the kick-off call during the sales close and make it clear that it is a step in setting up their account.

*These Customer Success posts are meant illustrate things we’ve learned at Proven, so they may not translate perfectly to your company / industry.  For context, the majority of our Saas customers are low LTV  “pro-sumers” who are generally SMBs*


How NOT to “Check In” With Your Customers

Ever emailed a customer something along the lines of “hey, just checking in”?
I know we definitely have.  In fact a lot of CS teams use this strategy to make sure they’re keeping track of your accounts statuses.  The idea behind it makes sense, you want to talk to your customers and make sure everything is running smoothly.
However, put yourself in the customer’s shoes.  If you’re busy running around handling 5 different tasks, do you want to pick up the phone only to hear “how’s everything going with our product?”.
Hell no, you have important things to do, plus you probably use a lot of different products.  That means that one company is just a small fraction of your tools.
We had scheduled “check-ins” throughout our customers journey, but we were noticing that people almost seemed irritated when we gave them a call (or were just awkward).  We then got a great piece of advice:
Only reach out to customers with a value add.
This could be fixing a problem, providing guidance, alerting them of a new feature, etc.  Make sure that when you contact them, you are delivering a benefit to them
We instantly found it was a lot easier to talk to people when we could tell them exactly WHY we were calling, and what the benefit to them was.
This type of check-in is best if it is driven by customer actions, not a pre-determined schedule.  This leads us to a whole different topic, which is creating a contextual alert system (great white paper from Totango) to drive your customer communications.
*These Customer Success posts are meant illustrate things we’ve learned at Proven, so they may not translate perfectly to your company / industry.  For context, the majority of our Saas customers are low LTV  “pro-sumers” who are generally SMBs*

How Do You Get More Customer Feedback? Bake It In Your Product

One of the first metrics we put in place for our customer success process is everyone’s favorite, the NPS score.

I know, I know, there could be debates for days on whether or not NPS is great, terrible, or somewhere in between.  For us, we decided it was a good way get a general temp of things, and more importantly to trigger proactive calls to customers who were happy or pissed.

We thought it would be this great source of insightful feedback and happily emailed thousands of users, excited to get all this great info!

We got 5 responses.  Whoop de do.

We had started to notice a trend at this time.  Our response rates for any type of feedback or outreach when we emailed was pretty dismal.  On the other hand, feature usage in the product was pretty solid, so the decision came to bake it into the product.

Response rate immediately jumped up by 30% and we got some really great pieces of feedback, as well as rescued some customers who were unhappy due to miscommunication and not knowing where certain features were.

Bottom line, if you want to collect any responses or interactions from your customers, build it into the product, don’t rely on email.

One caveat, no one likes to jump through a bunch of hoops, so limit the number of feedback mechanisms in your product to the essential ones.

*These Customer Success posts are meant illustrate things we’ve learned at Proven, so they may not translate perfectly to your company / industry.  For context, the majority of our Saas customers are low LTV  “pro-sumers” who are generally SMBs*

Resist the urge to develop on iOS (first)

Most people won’t heed this advice, hell, we basically didn’t, but I’m an optimist, so I’ll give it anyways.

Smaller startups, those with limited bandwidth and money, that are creating a consumer mobile product should start on Android, every time.

iOS-VS-Android (1)

Full disclosure is that I am not a developer, just a growth guy who works very closely with developers, so my opinion is coming from my experience as well as our dev team’s.  Most companies will start with iOS.  It’s sexy, it’s what most people talk about and it’s what they own.  Granted, there are very good reason to start with iOS (the fact that most startups are iOS users is a big one, I’m an iOS user and would be at a loss with initial Android design), but the thrust of my opinion comes from one big reason:  Iteration

As a lot of people know, startups thrive off speed and iteration.  There is already a lot of quality writing about running lean, so I won’t bore you, lets just agree that lean is good.

It is VERY difficult to iterate with iOS.  A lot of startups are still trying to perfect their product market fit and need to be able to make changes quickly as they optimize, other startups have their product but need to increase their conversions and want to be able to test on a rapid schedule.  Developing for iOS limits your flexibility and speed, a tradeoff I don’t believe is worth it.  Now when you’re still in development and are testing internally or bringing in a few testers, you can make changes just as quickly as Android, but the problems start to arise when you need fast, quality data.

First off, let’s say you want to get 30 beta testers to bang on your app so you can get some baseline stats.  You could go on Taskrabbit and hire people to come in, but it’d probably be a lot easier to use a mailing list or some other means of finding people online.  Now how do you distribute the dev version?  Testflight is great, but have you ever tried to get the average user to get through the onboarding sequence?  It’s a nightmare and a large time sink.  Between guiding users through the multiple steps, sending out new builds and constant updates, it easily becomes a full time job.  On Android?  Post a link to an APK, done.

Ok, so you ground through the testing process, got some killer feedback (but spent some precious $ and time) and you’re ready to push to the app store.  You did some decent launch marketing and you’re getting some installs and user data, but now you’ve found some areas that need improving.  Lets say you want to improve a signup form but you have two different designs.  The next step would be to split test them and see if you can optimize.  Unfortunately with Apple’s approval process you need to re-submit the app and wait roughly 5 days for approval and can only have one update in the queue.  This means that you will have to wait the time, test one form, then resubmit with the second form and wait longer.  On Android?  A few hours to push your new version.  Sure you could get beta testers to go over the forms, but beta users are inherently tainted because their motivations are changed the second they know they are testers.  You want the pure data that comes from real users.

There are a few services that offer A/B testing for native apps such as Pathmapp and Apptimize.  These services are great and allow you to change content without having to resubmit the app.  These can get pricey quick and may not be the best for a bootstrapped startup, also they require some extra work for simple tests.

If a company has the tools and ability to develop both, great, you can test on Android and then update to iOS.  If your app functionally makes more sense on iOS then this isn’t the best idea.  There are plenty of reasons not to start on Android.  Look, I’m an avid Apple user and I prefer their products over Android and other operating systems.  I’m just saying you should think about it.

So that’s where I stand.  I may not be right, but from personal experience and in regards to iteration and mobility, we’ve been kicking ourselves for constraining our testing to Apple’s approval schedule.  If we were to do it again we would start with Android and I think you should consider it too.

Good Hardware, Bad Software

The idea of this post came about when I was using my girlfriend’s dad’s new Samsung smartTV. The thing looks beautiful, it’s 55″, thin as a razor, and has a great picture. The box and manual both tout the ability to be connected online via cable or wifi and surf the web, to download Netflix, Pandora, and a host of other apps, and to generally never have to leave your couch for anything. To assist you in your one stop internet needs, the tv comes with a remote as well as a wireless keyboard with built in touchpad. I was helping him set things up and was marveling at the quality of the tv, the depth of the colors, the aesthetics of the design, etc etc.

Once we had the thing physically set up, cables and all, came the part where I would connect to wireless and download all the fun apps. At this point I felt like I was trying to walk through mud and my hands had been replaced by those huge foam hulk hands.


The culprit was the software, it was just BAD.  It was clunky, not very intuitive, the UI was jumbled, and it really gave me, someone who thinks of himself as technically proficient (though I’m probably not), a decent amount of trouble.  It got me thinking about the quality standard of software and how it relates to hardware.  The focal point for tvs is still on the hardware.  People want thin, they want big, they want a great picture, they want cheaper, and they want connectivity.  This Samsung checked all those boxes (maybe not cheaper) pretty well, and really was some great hardware.  I think that really good hardware can still forgive bad software in some cases, especially when it does new things.  Obviously the smart tv industry is just getting started, and there is a lot of room for growth in software interfaces, but I was surprised by how bad it was.

The idea for this post was solidified when Apple released iOS 7 recently.  I’ve played around with it a bit, and I think it’s a great redesign, and a good example of how Apple has used great software to complement their hardware.  Though they have obviously been huge innovators in consumer electronics and hardware, it has been their software experience that has set them apart as a great product.


We’re going to be getting to the point where the competing hardware sets (be it phone, tv, computer) are more and more similar and the differentiator is the software.  I’ve formed the opinion now that Apple can make a strong move into the TV space and have a pretty large impact.  I’ve always felt they were going to do this, but I wasn’t sure how innovative they would be, and how successful.  Their name alone will sell units, but I couldn’t really think of how they would blow the smart tv game wide open.  I still don’t think they will, but I think there is enough to make better on the software side, that they can easily become a market force.  Now I haven’t used too many other smart tvs and I may be missing a great set, but from personal experience there is a lot of room for improvement.

Conference Inspiration

Are conferences, events, conventions, etc worth the time or money?


I’ve long had the attitude that conferences or conventions held little value for me or most of the attendees. Aside from a networking opportunity or possibly the chance to get on stage, I couldn’t justify the cost to attend. As someone who does user growth at startups, I looked at the money spent on a ticket as hundreds of lost users that could teach me boat loads more than the speakers I was going to listen to, or at least pretend to listen to.

Now I understand that the same is not for everyone, and I’m quite possibly in the minority. People find a lot of value at these things and generally seem to enjoy them. If they didn’t, there wouldn’t be any demand for these things (duh, Alex).

Last week I went to the Game Designers Conference here in SF and it really has changed my thinking on these types of events.  First off, I have to give props to the conference organizers.  Not only did everything run smoothly and have a great feeling of cohesion, but the content and speakers were pretty great considering there were over 100 different talks the whole week.  I had originally balked at the idea of attending for some of the afore-mentioned reasons, and had already kinda expected the whole thing to suck.   As the week went on, I felt more and more invigorated.  Talking with our team I found that everyone had started feeling the same way.  Being surrounded by people who are DOING things, creating things, sharing things is really an inspiration.  Being in that type of atmosphere can really be a shot in the arm for ones own career.  This conference’s value to me was not necessarily from the talks, the networking, or the demos, it was from the motivation and drive that I got from being in close proximity to so many people that are excited about doing what they love.

So take pessimists like me with a grain of salt when thinking about attending these things.  Make sure you are going for the right reasons, and keep yourself open to the inspirations around you.  The benefits can often be immeasurable and unquantifiable.  For us, it brought new life to our team and our vision and I will definitely return next year (plus it’s pretty sweet to play a bunch of video games for “work”).


PS.  Go to the parties if for nothing else than to have fun.  We got to go to Mojang’s Skrillex and Diplo concert and it was fuckin’ awesome!  Really put a bow on the whole experience (and a hangover).